Synthesis of Novel Anthracene Crown Ethers and the Guest Binding Behaviors†

doi:10.7503/cjcu20170317

Abstract

Abstract:

Two crown ethers bearing anthracene aromatics were synthesized from 9,10-dibromomethyl anthracene via three steps. The host-guest binding behavior between new crown ethers and two π-electron-deficient guests was investigated by means of ¹H NMR, UV-Vis spectroscopy and X-ray diffraction analysis. The results revealed that host-guest interaction between anthracene crown ethers and guests was mainly contributed by π-stacking. The association constants determined by UV-Vis spectrum. The result showed anthracene crown ethers had better binding ability than classical bezo- and naphtho-crown ethers, which indicated the introduction of anthracene aromatics could improve the host-guest binding ability of crown ethers significantly.

Key words: Anthracene, Crown ether, Host-guest binding, π-Stacking interaction

CLC Number:

O625

TrendMD:

FANG Qiusheng, LI Yanhong, CHEN Ling. Synthesis of Novel Anthracene Crown Ethers and the Guest Binding Behaviors^†[J]. Chem. J. Chinese Universities, 2017, 38(9): 1563.

Figures/Tables 4

Scheme 1 Synthetic route of the crown ethers 1 and 2 and structures of guest molecules MV and MP

Fig.1 Partial 1H NMR spectra(400 MHz, CD3CN, 25 ℃) of compound 1(a), MV and compound 1(b), MV(c), MV and compound 2(d), compound 2(e)

Fig.2 Host-guest UV-Vis titration of complex 1(1 mmol/L) with MV(a—j: 0, 0.2, 0.4, 0.6, 0.8, 1, 1.5, 2, 3, 5 mmol/L) in MeCN at 25 ℃(A) Absorption spectra; (B) nonlinear least-squares analysis of the absorption intensity at 480 nm to calculate the association

Fig.3 Top(A, B) and side(C, D) views of crystal structures for the complexes of MP?1(A, C) and MP?2(B, D) Solvent molecules, counter ions and partial hydrogen atoms are omitted for clarity.

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